AR035884A1 - DERIVED FROM AROMATIC AMIDA REPLACED, DERIVED FROM AROMATIC AMINA REPLACED WITH A USEFUL FLUOROALKYL GROUP AS AN INTERMEDIARY TO OBTAIN THE SAME, INSECTICIATED FOR AGROHORTICULTURE THAT CONTAINS AND METHOD TO USE THIS LAST - Google Patents

DERIVED FROM AROMATIC AMIDA REPLACED, DERIVED FROM AROMATIC AMINA REPLACED WITH A USEFUL FLUOROALKYL GROUP AS AN INTERMEDIARY TO OBTAIN THE SAME, INSECTICIATED FOR AGROHORTICULTURE THAT CONTAINS AND METHOD TO USE THIS LAST

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Publication number
AR035884A1
AR035884A1 ARP020101711A ARP020101711A AR035884A1 AR 035884 A1 AR035884 A1 AR 035884A1 AR P020101711 A ARP020101711 A AR P020101711A AR P020101711 A ARP020101711 A AR P020101711A AR 035884 A1 AR035884 A1 AR 035884A1
Authority
AR
Argentina
Prior art keywords
group
alkyl
haloalkyl
different
same
Prior art date
Application number
ARP020101711A
Other languages
Spanish (es)
Inventor
Makoto Goto
Minoru Yamaguchi
Hiroto Harayama
Hayami Nakao
Takashi Furaya
Masanori Tohnishi
Masayuki Morimoto
Shinsuke Fujioka
Original Assignee
Nihon Nohyaku Co Ltd
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Publication date
Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd
Publication of AR035884A1 publication Critical patent/AR035884A1/en

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/16—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
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    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/85—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic unsaturated carbon skeleton
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    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
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    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
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    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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  • Organic Chemistry (AREA)
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  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

Un derivado de amida aromático sustituido representado por la fórmula general (1), {donde Z representa la fórmula (2) (donde A, R1, y R2 son tal como se definen a continuación), o la fórmula (3) (donde A representa un grupo alquileno C1-6; un grupo alquileno C1-6 sustituido que tiene al menos un sustituyente igual o diferente seleccionado del grupo que consiste en átomo de halógeno, grupo ciano, nitro, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, alquiltio C1-6-alquilo C1-6, alcoxicarbonilo C1-6 y fenilo; un grupo alquenileno C2-6; un grupo alquenileno C2-6 sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en átomo de halógeno, grupo ciano, nitro, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, alquiltio C1-6-alquilo C1-6, alcoxicarbonilo C1-6 y fenilo; un grupo alquinileno C2-6; o un grupo alquinileno C3-6 sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en átomo de halógeno, grupo ciano, nitro, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, alquiltio C1-6-alquilo C1-6, alcoxicarbonilo C1-6 y fenilo; y un átomo de carbono saturado seleccionado arbitrariamente en el grupo alquileno C1-6, alquileno C1-6 sustituido, alquenileno C3-6, alquenileno C3-6 sustituido, alquinileno C3-6 o alquinileno C3-6 sustituido pueden estar sustituidos por un grupo alquileno C2-5 para formar un anillo cicloalcano C3-6, y dos átomos de carbono seleccionados arbitrariamente en el grupo alquileno C2-6, alquileno C2-6 sustituido, alquenileno C3-6 o alquenileno C3-6 sustituido pueden tomarse en conjunto con un grupo alquileno o un grupo alquenileno para formar un anillo cicloalcano C3-6 o un anillo cicloalqueno C3-6; R1 representa un hidrógeno, halógeno, ciano, nitro, cicloalquilo C3-6, alcoxicarbonilo C1-6, monoalquilaminocarbonilo C1-6, dialquilaminocarbonilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, monoalquilaminosulfonilo C1-6, dialquilaminosulfonilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, dialcoxifosforilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, dialcoxitiofosforilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, -C(R5)=NOR6 (donde R5 representa hidrógeno o alquilo C1-6; y R6 representa hidrógeno, alquilo C1-6, alquenilo C3-6, alquinilo C3-6, cicloalquilo C3-6, fenilalquilo C1-4, o un grupo fenilalquilo C1-4 sustituido que tiene, en el anillo del mismo, al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6 y alquiltio C1-6), fenilo, fenilo sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; heterocíclico, heterocíclico sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; o -A1-R7 (donde A1 representa -O-, -S-, -SO-, -SO2- ó -N(R6)-; y R7 representa hidrógeno, alquilo C1-6, haloalquilo C1-6, alquenilo C3-6, haloalquenilo C3-6, alquinilo C3-6, haloalquinilo C3-6, cicloalquilo C3-6, fenilo, fenilo sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6 y alcoxicarbonilo C1-6; fenilalquilo C1-4, fenilalquilo C1-4 sustituido que tiene, en el anillo del mismo, al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6 y alcoxicarbonilo C1-6; heterocíclico, heterocíclico sustituido que tiene, en el anillo del mismo, al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6 y alcoxicarbonilo C1-6; alquilcarbonilo C1-6, haloalquilcarbonilo C1-6, alcoxicarbonilo C1-6, monoalquilaminocarbonilo C1-6, dialquilaminocarbonilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, monoalquilaminosulfonilo C1-6, dialquilaminosulfonilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, alcoxifosforilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, o alcoxitiofosforilo C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes); R2 representa un átomo de hidrógeno, un grupo alquilo C1-4, alcoxi C1-4-alquilo C1-4, o alquiltio C1-4-alquilo C1-4; y R2 puede tomarse junto con A o R1 para formar 1 a 3 anillos de 5 a 7 miembros, iguales o diferentes, que pueden estar interceptados por un átomo de oxígeno, azufre o nitrógeno); R3 representa un átomo de hidrógeno, un grupo alquilo C1-4, alcoxi C1-4-alquilo C1-4, o alquiltio C1-4-alquilo C1-4; R4 representa hidrógeno, flúor, o fluoroalquilo C1-6; y Rf representa flúor o fluoroalquilo C1-6; Q1 a Q9, los cuales pueden ser iguales o diferentes, representan un átomo de carbono o un átomo de nitrógeno; X los cuales pueden ser iguales o diferentes, representan halógeno, nitro, ciano, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, o haloalquilsulfonilo C1-6; y dos grupos de X que residen en posiciones adyacentes en el anillo aromático pueden tomarse en conjunto para formar un anillo fundido, y dicho anillo fundido puede tener al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; y l representa un número entero de 0 a 2; Y que puede ser igual o diferente, representa halógeno, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-6, alcoxi C1-6, haloalcoxi C1-6, monoalquilamino C1-6, dialquilamino C1-6 cuyos grupos alquilo C1-6 pueden ser iguales o diferentes, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, fenilo, fenilo sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste de halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; fenilalquilo C1-6, fenilalquilo C1-6 sustituido que tiene, en el anillo del mismo, al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; fenoxi, fenoxi sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; feniltio, feniltio sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; un grupo heterocíclico, o heterocíclico sustituido que tiene al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste de halógeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; y dos grupos de Y que residen en posiciones adyacentes en el anillo aromático pueden tomarse en conjunto para formar un anillo fundido, y dicho anillo fundido puede tener al menos un sustituyente, igual o diferente, seleccionado del grupo que consiste en halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6 y haloalquilsulfonilo C1-6; e Y puede tomarse junto con R3 para formar un anillo de 5 a 7 miembros que puede estar interceptado por uno o dos átomos de oxígeno, azufre o nitrógeno, iguales o diferentes; y m representa un número entero de 0 a 3}. Derivado de amina aromático sustituido con un grupo fluoroalquilo útil como intermediario para obtener un derivado de amida anteriormenA substituted aromatic amide derivative represented by the general formula (1), {where Z represents the formula (2) (where A, R1, and R2 are as defined below), or the formula (3) (where A represents a C1-6 alkylene group; a substituted C1-6 alkylene group having at least one equal or different substituent selected from the group consisting of halogen atom, cyano group, nitro, C1-6 haloalkyl, C1-6 alkoxy, haloalkoxy C1-6, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 alkylthio-C1-6 alkyl, C1-6 alkoxycarbonyl and phenyl ; a C2-6 alkenylene group; a substituted C2-6 alkenylene group having at least one substituent, the same or different, selected from the group consisting of halogen atom, cyano group, nitro, C1-6 haloalkyl, C1-6 alkoxy , C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, alkylsulfonyl C 1-6, C 1-6 haloalkylsulfonyl, C 1-6 alkylthio-C 1-6 alkyl, C 1-6 alkoxycarbonyl and phenyl; a C2-6 alkynylene group; or a substituted C3-6 alkynylene group having at least one substituent, the same or different, selected from the group consisting of halogen atom, cyano group, nitro, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, alkylthio C1-6, haloalkylthio C1-6, alkylsulfinyl C1-6, haloalkylsulfinyl C1-6, alkylsulfonyl C1-6, haloalkylsulfonyl C1-6, alkylthio C1-6-alkyl C1-6, alkoxycarbonyl C1-6 and phenyl; and a saturated carbon atom arbitrarily selected in the group C1-6 alkylene, substituted C1-6 alkylene, C3-6 alkenylene, substituted C3-6 alkenylene, C3-6 alkynylene or substituted C3-6 alkynylene may be substituted by an alkylene group C2-5 to form a C3-6 cycloalkane ring, and two arbitrarily selected carbon atoms in the C2-6 alkylene, substituted C2-6 alkylene, C3-6 alkenylene or substituted C3-6 alkenylene group can be taken together with a group alkylene or an alkenylene group to form a C3-6 cycloalkane ring or a C3-6 cycloalkene ring; R1 represents hydrogen, halogen, cyano, nitro, C3-6 cycloalkyl, C1-6 alkoxycarbonyl, C1-6 monoalkylaminocarbonyl, C1-6 dialkylaminocarbonyl whose C1-6 alkyl groups may be the same or different, C1-6 monoalkylamino sulfonyl, C1- dialkylaminosulfonyl 6 whose C1-6 alkyl groups may be the same or different, C1-6 dialkoxyphosphoryl whose C1-6 alkyl groups may be the same or different, C1-6 dialkoxythiophosphoryl whose C1-6 alkyl groups may be the same or different, -C (R5) = NOR6 (where R5 represents hydrogen or C1-6 alkyl; and R6 represents hydrogen, C1-6 alkyl, C3-6 alkenyl, C3-6 alkynyl, C3-6 cycloalkyl, C1-4 phenylalkyl, or a C1-4 phenylalkyl group substituted which has, in the ring thereof, at least one substituent, the same or different, selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy and C1-6 alkylthio), phenyl, substituted phenyl having at least one substituent, the same or different, selected from the group consisting of halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkyl, C 1-6 alkylsulfonyl and C 1-6 haloalkylsulfonyl; heterocyclic, substituted heterocyclic having at least one substituent, equal or different, selected from the group consisting of halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1- alkylthio 6, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; or -A1-R7 (where A1 represents -O-, -S-, -SO-, -SO2- or -N (R6) -; and R7 represents hydrogen, C1-6 alkyl, C1-6 haloalkyl, C3 alkenyl- 6, C3-6 haloalkenyl, C3-6 alkynyl, C3-6 haloalkynyl, C3-6 cycloalkyl, phenyl, substituted phenyl having at least one substituent, equal or different, selected from the group consisting of halogen, cyano, nitro, alkyl C1-6, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl and alkoxycarbonyl C1-6; C1-4 phenylalkyl, substituted C1-4 phenylalkyl having, in the ring thereof, at least one substituent, the same or different, selected from the group consisting of halogen, cyano, nitro, C1-6 alkyl, haloalkyl C1-6, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl and C1-6 alkoxycarbonyl; heterocyclic , substituted heterocyclic having, in the ring thereof, at least one substituent, equal or different, selected from the group consisting of halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1 haloalkoxy -6, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl and C1-6 alkoxycarbonyl; C1-6 alkylcarbonyl, C1-6 haloalkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 monoalkylaminocarbonyl, C1-6 dialkylaminocarbonyl whose C1-6 alkyl groups may be the same or different, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 monoalkylaminosulfonyl , C1-6 dialkylaminosulfonyl whose C1-6 alkyl groups may be the same or different, C1-6 alkoxyphosphoryl whose C1-6 alkyl groups may be the same or different, or C1-6 alkoxythiophosphoryl whose C1-6 alkyl groups may be the same or different) ; R2 represents a hydrogen atom, a C1-4 alkyl group, C1-4 alkoxy-C1-4 alkyl, or C1-4 alkylthio-C1-4 alkyl; and R2 may be taken together with A or R1 to form 1 to 3 rings of 5 to 7 members, the same or different, which may be intercepted by an oxygen, sulfur or nitrogen atom); R3 represents a hydrogen atom, a C1-4 alkyl group, C1-4 alkoxy-C1-4 alkyl, or C1-4 alkylthio-C1-4 alkyl; R4 represents hydrogen, fluorine, or C1-6 fluoroalkyl; and Rf represents fluorine or C1-6 fluoroalkyl; Q1 to Q9, which may be the same or different, represent a carbon atom or a nitrogen atom; X which may be the same or different, represent halogen, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, C 1-6 alkoxy , C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, or C1-6 haloalkylsulfonyl; and two groups of X residing in adjacent positions in the aromatic ring may be taken together to form a molten ring, and said molten ring may have at least one substituent, the same or different, selected from the group consisting of halogen, cyano, nitro , C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl ; and l represents an integer from 0 to 2; And which may be the same or different, it represents halogen, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 monoalkylamino, C 1-6 dialkylamino whose C 1-6 alkyl groups 6 may be the same or different, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, phenyl, substituted phenyl having at least one substituent, equal or different, selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkyl, C 1-6 alkylsulfonyl and C 1-6 haloalkylsulfonyl; C1-6 phenylalkyl, substituted C1-6 phenylalkyl having, in the ring thereof, at least one substituent, the same or different, selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy , C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; phenoxy, substituted phenoxy having at least one substituent, the same or different, selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1 haloalkyl -6, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; phenylthio, substituted phenylthio having at least one substituent, the same or different, selected from the group consisting of halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1 haloalkyl -6, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; a heterocyclic, or substituted heterocyclic group having at least one substituent, the same or different, selected from the group consisting of halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; and two groups of Y residing in adjacent positions in the aromatic ring may be taken together to form a molten ring, and said molten ring may have at least one substituent, the same or different, selected from the group consisting of halogen, C1- alkyl 6, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl and C1-6 haloalkylsulfonyl; and Y can be taken together with R3 to form a 5 to 7 member ring that can be intercepted by one or two oxygen, sulfur or nitrogen atoms, the same or different; and m represents an integer from 0 to 3}. Aromatic amine derivative substituted with a fluoroalkyl group useful as an intermediate to obtain an amide derivative above

ARP020101711A 2001-05-18 2002-05-10 DERIVED FROM AROMATIC AMIDA REPLACED, DERIVED FROM AROMATIC AMINA REPLACED WITH A USEFUL FLUOROALKYL GROUP AS AN INTERMEDIARY TO OBTAIN THE SAME, INSECTICIATED FOR AGROHORTICULTURE THAT CONTAINS AND METHOD TO USE THIS LAST AR035884A1 (en)

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